Tetrahydrofuran → N-(4-Chloro-2-cyanophenyl)-2-(5-morpholin-4ylbenzimidazol-2-yl)acetamide

LiHMDS (2.5 eq) was added to ethyl 2-[5-(2-morpholin-4-ylethoxy)benzimidazol-2-yl]acetate (1.0 eq) in THF at −78° C. After 1 hour, 2-amino-5-chlorobenzenecarbonitrile (0.82 eq) in THF was added. The reaction was allowed to warm to 23° C. and stirred overnight. The resulting mixture was quenched with NH4Cl (aqueous saturated solution) and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo to yield a brown solid. The crude material was purified by silica gel chromatography (5:1 EtOAc:hexane) to give the desired product. LC/MS m/z 396.1 (MH+), Rf 1.79 minutes.

1. customThe resulting mixture was quenched with NH4Cl (aqueous saturated solution)
2. extractionextracted with EtOAc
3. washThe combined organic layers were washed with H2O and brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto yield a brown solid
8. customThe crude material was purified by silica gel chromatography (5:1 EtOAc:hexane)

ORD-Eintrag

ord-31fb1ab8829c49f191a7f1634835eb16

Quelldatensatz

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06605617B2